Daptomycin

Summary

Daptomycin (CHEMBL387675) is an approved small-molecule antibacterial drug (ATC J01XX09); indicated across 21 conditions including bacterial infectious disease with sepsis and bacterial endocarditis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01XX09
• Indications: 21 conditions
• Clinical trials: 81
• Chemistry: 1620.7 Da · C72H101N17O26

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL387675
Name	Daptomycin
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	16134395
ChEBI	CHEBI:600103
ATC	J01XX09
Molecular formula	C72H101N17O26
Molecular weight	1620.7
InChIKey	DOAKLVKFURWEDJ-RWDRXURGSA-N

SMILES: CCCCCCCCCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]3[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C

IUPAC name: (3S)-3-[[(2S)-4-amino-2-[[(2S)-2-(decanoylamino)-3-(1H-indol-3-yl)propanoyl]amino]-4-oxobutanoyl]amino]-4-[[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriacont-30-yl]amino]-4-oxobutanoic acid

ChEBI definition: A polypeptide comprising N-decanoyltryptophan, asparagine, aspartic acid, threonine, glycine, ornithine, aspartic acid, D-alanine, aspartic acid, glycine, D-serine, threo-3-methylglutamic acid and 3-anthraniloylalanine (also known as kynurinine) coupled in sequence and lactonised by condensation of the carboxylic acid group of the 3-anthraniloylalanine with the alcohol group of the threonine residue.

Pharmacological roles (ChEBI): antibacterial drug, calcium-dependent antibiotics.

Other ChEBI roles (chemical / environmental): bacterial metabolite.

Also known as: Cidecin, Cubicin, Cubicin rf, Dapcin, Daptomicina, Daptomycin, Daptomycin hospira, Daptomycine, Dapzura rt, LY 146032, LY-146032, LY-164032

Patent coverage: 5,894 distinct patent families (19,735 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 19,618 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: ATP-binding cassette sub-family C member 2.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

21 indications (9 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
bacterial infectious disease with sepsis	4	MONDO:0005229	EFO:0003033
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
bacterial endocarditis	4	MONDO:0006669	EFO:1000830
endocarditis	4	MONDO:0005025	MONDO:0000565
gram-positive bacterial infections	4	MONDO:0021679	MONDO:0021679
skin disease caused by bacterial infection	4	MONDO:0024295	MONDO:0024295
osteomyelitis	3	MONDO:0005246	EFO:0003102
skin disorder	3	MONDO:0005093	EFO:0000701
staphylococcus aureus infection	3	MONDO:0005545	EFO:0005681
bacterial pneumonia	3	MONDO:0004652	EFO:1001272
kidney failure	3	MONDO:0001106	EFO:1002048
nosocomial infection	3	MONDO:0043544	MONDO:0043544
pneumococcal meningitis	2	MONDO:0006913	EFO:1001114
hematopoietic and lymphoid system neoplasm	2	MONDO:0002334	MONDO:0044881
chronic kidney disease	1	MONDO:0005300	EFO:0003884
meningitis	1	MONDO:0021108	MONDO:0021108

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 81.

Phase distribution

Phase	Trials
PHASE4	25
PHASE3	18
PHASE2	16
Not specified	11
PHASE1	9
PHASE2/PHASE3	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06637332	PHASE4	RECRUITING	Daptomycin vs. Vancomycin for the Treatment of Methicillin Resistant S. Aureus Bacteremia
NCT00295178	PHASE4	COMPLETED	Study Comparing CUBICIN® (Daptomycin for Injection) With Vancomycin in Cellulitis or Erysipelas
NCT00401960	PHASE4	TERMINATED	Daptomycin as an Adjuvant Agent in the Treatment of Enterococcal Native Valve Endocarditis.
NCT00463801	PHASE4	TERMINATED	Safety and Efficacy of Daptomycin for the Treatment of Complicated Skin and Skin-structure Infections
NCT00572260	PHASE4	TERMINATED	A Pilot Study of Daptomycin for Antimicrobial Prophylaxis
NCT00638157	PHASE4	TERMINATED	Phase 4 Efficacy and Safety Study of Cubicin® With and Without Combination Therapy in S. Aureus Infective Endocarditis (SAIE)
NCT00651131	PHASE4	TERMINATED	Cubicin(R) for Complicated Post-surgical Wound Infections
NCT00663403	PHASE4	COMPLETED	Pharmacokinetics of Daptomycin in Critically Ill Patients Receiving Continuous Venovenous Hemodialysis (CVVHD)
NCT00711802	PHASE4	COMPLETED	Safety and Efficacy Study of Daptomycin in Pediatric Participants (1 to 17 Years-old) With Skin and Skin Structure Infections
NCT01080963	PHASE4	COMPLETED	Daptomycin as Antibiotic Prophylaxis of Sternal Wound Infections
NCT01104662	PHASE4	TERMINATED	Study of Daptomycin Safety and Efficacy for Complicated Skin and Skin Structure Infections (cSSSI) and Bacteremia in Renal Impairment
NCT01133600	PHASE4	TERMINATED	Outpatient Treatment of Gram Positive Wound Infections in the Diabetic Foot: A Pharmaco-economic Comparison of Daptomycin vs. Vancomycin Based Regimens
NCT01175707	PHASE4	TERMINATED	Study Comparing Cubicin With Vancomycin in Treatment of Participants With Complicated Skin and Skin Structure Infections in a Home Infusion Setting
NCT01196169	PHASE4	TERMINATED	Daptomycin Use for Antimicrobial Prophylaxis in Methicillin Resistant Staphylococcus Aureus (MRSA) Colonized Adult Patients Undergoing Primary Elective Hip, Knee, or Shoulder Arthroplasty
NCT01287832	PHASE4	TERMINATED	Vancomycin Versus Daptomycin for the Treatment of Methicillin-resistant Staphylococcus Aureus Bacteremia Due to Isolates With High Vancomycin Minimum Inhibitory Concentrations (MICs)
NCT01419184	PHASE4	COMPLETED	Daptomycin Versus Vancomycin in Participants With Skin Infections Due to MRSA
NCT01549613	PHASE4	COMPLETED	Evaluation of Daptomycin for the Emergency Department Treatment of Complicated Skin and Skin Structure Infections
NCT01626560	PHASE4	COMPLETED	The Effects of Daptomycin and Cytokines Production in Comparison With Vancomycin
NCT01728376	PHASE4	COMPLETED	Safety & Efficacy of Daptomycin Versus Standard of Care (SOC) in 1 - 17 Year Olds With Staphylococcus Aureus Bacteremia (MK-3009-005)
NCT01734694	PHASE4	TERMINATED	Safety and Efficacy of Strategy to Prevent Drug-Induced Nephrotoxicity in High-Risk Patients
NCT02241941	PHASE4	WITHDRAWN	Evaluation of Single-dose Pharmacokinetics of Intravenous Daptomycin in Patients With Thermal Injury
NCT02660346	PHASE4	COMPLETED	IL-10 Stratifying Tool for Towards Antibiotic Selection for MRSaB
NCT02972983	PHASE4	COMPLETED	Daptomycin as Adjunctive Therapy for Staphylococcus Aureus Bacteremia
NCT05156437	PHASE4	TERMINATED	Postoperative Antibiotic Management Duration Following Surgery for Intravenous Drug Abuse (IVDA) Endocarditis (OPTIMAL)
NCT05977868	PHASE4	TERMINATED	Comparing Oral Versus Parenteral Antimicrobial Therapy
NCT00055198	PHASE3	TERMINATED	Daptomycin for the Treatment of Infections Due to Gram-Positive Bacteria
NCT00093067	PHASE3	COMPLETED	Daptomycin in the Treatment of Subjects With Infective Endocarditis or Bacteremia Due to S. Aureus
NCT00430937	PHASE3	TERMINATED	Efficacy and Safety of Daptomycin Versus Vancomycin or Teicoplanin for Treatment of Complicated Skin and Soft Tissue Infections
NCT00538694	PHASE3	COMPLETED	Comparative Study of Cidecin™ (Daptomycin) to Rocephin® (Ceftriaxone) in the Treatment of Moderate to Severe Community-Acquired Acute Bacterial Pneumonia
NCT00540072	PHASE3	COMPLETED	Study of Cidecin™ (Daptomycin) to Rocephin® (Ceftriaxone) in the Treatment of Moderate to Severe Community-Acquired Acute Bacterial Pneumonia Due to S. Pneumoniae
NCT00701636	PHASE3	COMPLETED	Pharmacokinetics of Daptomycin During Cardiopulmonary Bypass Surgery
NCT00770341	PHASE3	COMPLETED	A Study of MK-3009 in Japanese Patients With Skin or Blood Stream Infections Caused by Methicillin-resistant Staphylococcus Aureus (MK-3009-002)
NCT00772447	PHASE3	COMPLETED	China Registration Study in Patients With Skin Infections
NCT01184872	PHASE3	COMPLETED	Study to Compare Efficacy and Safety of Daptomycin in Elderly Patients With Complicated Skin and Soft Tissue Infections
NCT01199783	PHASE3	TERMINATED	Application of Daptomycin in MRSA Infected Diabetic Foot in Comparison to Vancomycin Treatment
NCT01216241	PHASE3	TERMINATED	Daptomycin Versus Placebo in Patients With Neutropenia and Fever
NCT01455246	PHASE2/PHASE3	TERMINATED	Daptomycin + Meropenem Versus Ceftazidime in the Treatment of Nosocomial Spontaneous Bacterial Peritonitis
NCT01515020	PHASE3	TERMINATED	Daptomycin Versus Vancomycin in the Treatment of Nosocomial or Healthcare-associated MRSA Bacteremia
NCT01792804	PHASE3	COMPLETED	Staphylococcus Aureus Bacteremia Antibiotic Treatment Options
NCT01898338	PHASE3	COMPLETED	Efficacy of Daptomycin Plus Fosfomycin Versus Daptomycin for Treatment of MRSA Bacteremia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).